Sulfone Projects

  • Sulfones and sulfonamides are attractive functional groups to leverage in the dearomatization of benzene for several reasons. Sulfur is the third most common heteroatom in marketed pharmaceuticals behind nitrogen and oxygen. Sulfones and sulfonamides are prevalent in a variety of antibiotics, cancer therapeutics, COX-2 inhibitors, diuretics, and ulcer preventatives. Further, unlike the previous electron deficient groups, sulfinates (:SO2R-) have been observed as leaving groups for nucleophilic substitution and elimination reactions, and this could significantly expand the diversity of the anticipated trisubstituted cyclohexene products beyond the anticipated sulfone and sulfonamide derivatives.

  • It was discovered that using bidentate ligands as nucleophiles the formation of multicyclic molecules was encouraged, due to the ability of sulfinates (:SO2R-) to act as leaving groups. This approach could significantly expand the diversity of the anticipated trisubstituted cyclohexene products beyond the anticipated sulfone derivatives, where additional structural complexity is introduced. As shown below, it can be envisioned the presence of bidentate ligands stemming from peptides or aminoacids moieties.